Stereoselective Synthesis

The state-of-the-art in stereoselective synthesis Thoroughly revised and updated, this enlarged second edition offers a plethora of valuable information on methods and reagents in stereoselective synthesis. Methods have been selected for high efficiency and selectivity; mechanistic aspects are treated succinctly, with a strong emphasis on practical applications. For this new edition, material has been added on * homogeneous diastereoselective hydrogenations * enantioselective oxidations * novel, efficient chiral auxiliaries Much of the information given is presented in figures and tables, which makes the book a valuable reference work for the practically minded organic chemist. From reviews of the first edition: 'The extensive material in the volume should prove particularly useful to anyone involved in synthetic chemistry or teaching a course in organic chemistry.' Journal of Medicinal Chemistry 'With nearly 1400 references cited, the book contains a wealth of information and should be a useful addition to the chemist's library.' The American Scientist

List of Symbols and Abbreviations Introduction 1 General Concepts of Stereoselective Synthesis 1.1 Principles of Differentiating Molecules 1.2 Characterization of Stereoisomers. Conformation and Configuration 1.3 Intramolecular Symmetry. Topicity and Prochirality 1.4 Selectivity in Chemistry 1.4.1 Substrate Selectivity 1.4.1.1 Substrate Diastereoselectivity (Diastereomer Selectivity) 1.4.1.2 Substrate Enantioselectivity (Enantiomer Selectivity). Kinetic Resolution 1.4.2 Product Selectivity 1.4.2.1 Formation of Stereoisomers 1.4.2.2 Conditions Necessary for Stereoselectivity 1.4.2.3 Concept of Stereodifferentiation 1.4.2.4 Niethods for Inducing Stereoselectivity 1.4.3 Stamelective Synthetic Strategies 1.4.3.1 Enandoconvergent Synthesis 1.4.3.2 Selective Preparation of Both Enantiomers from a Single Substrate 1.5 Kinetics and Thermodynamics of Stereoselective Reactions Stereoselective Catalytic Reductions 2.1 Stereoselective Homogeneous Hydrogenations with Rhodium-. Ruthenium- and Iridium-Phosphine Catalysts 2. 1. 1 Hydrogenation of Olefinic Bonds 2.1.1.1 Chiral Phosphorus Containing Ligands 2.1.2 Enantioselective Catalytic Hydrogenation of Ketones and Imines 2.1.3 Diastereoselective Hydrogenations in Homogeneous Phase 2.2 Catalytic Hydrosilylation 2.3 Heterogeneous Stereoselective Catalytic Hydrogenations 2.3.1 Enantioselective Heterogeneous Catalytic Hydrogenations 2.3.2 Diastereoselective Heterogeneous Catalytic Hydrogenations 3 Stercoselective Non-Catalytic Reduction 3. 1 Enantioselective Reductions 3.1.1 Chiral Lithium Aluminum Hydrides 3.1.1.1 Reduction of Carbonyl Groups 3.1.1.2 Reduction of C=N and C=C Bonds 3.1.2 Chirally Modified Hydroborates 3.1.3 Chiral Boranes and Boronates 3.1.4 Enantioselective Reductions with Hydride Transfer from Carbon 3.1.4.1 Chiral Trialkyl Boranes 3.1.4.2 Chiral Metal Alkyls 3.1.4.3 Chiral Metal Alkoxides 3.1.4.4 Chiral 1,4-Dihydropyridines 3.1.5 Correlation of Substrate Constitution and Enantioselectivity 3.2 Diastereoselective Reduction of Carbonyl Groups 3.2.1 Stereochemistry of Diastereoselective Ketone Reduction 3.2.2 Practical Aspects of Diastereoselective Ketone Reductions 4 Stercoselective Oxidations 4.1 Enandoselective Oxidations 4.1.1 Epoxidadon with Chiral Oxidants 4.1.2 Oxidations in the Presence of Chiral Catalysts 4.2 Diastereoselective Oxidations 4.2. 1 Diastereoselective Epoxidation 4.2.2 Various Diastereoselective Oxidations 5 Stereoselective Carbon-Carbon Bond Forming Reactions by Nucleophilic A ddition to Carbonyl Groups 5.1 Addition of Simple Nucleophiles to Carbonyl Compounds 5. 1. 1 Enantioselective Additions 5.1.2 Diastereoselective Additions 5.1.3 Additions to C=N Bonds 5.2 Addition Involving Allylmetal and Allylboron Compounds 5.2.1 General Aspects of Allylmetal Addition 5.2.2 Addition of Alkylboron Compounds 5.2.3 Addition of Allyltitaniurn Compounds 5.2.4 Addition of Allylsilanes 5.2.5 Addition of Allyistannanes

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